title: [2,3]-Sigmatropic rearrangements of 3-sulfinyl dihydropyrans: application to the syntheses of the cores of ent-dysiherbaine and deoxymalayamicin A.
abstract: The [2,3]-sigmatropic rearrangement of a variety of configurationally stable diastereomeric allylic sulfinyl dihydropyrans, produced by base-promoted cyclization of sulfinyl dienols, has been studied. In some cases, the efficient transformation of these substrates into dihydropyranols required an in-depth study of reaction conditions, with the preferred protocol relying on the use of DABCO in warm toluene. This methodology has been applied to the syntheses of the cores of ent-dysiherbaine and deoxymalayamicin A by means of efficient tethered aminohydroxylations.
authors.affiliation: Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain. iqofp19@iqog.csic.es
authors.forename: Roberto
authors.initials: R
authors.lastname: Fernández de la Pradilla
authors.forename: Nadia
authors.initials: N
authors.lastname: Lwoff
authors.forename: Miguel Angel
authors.initials: MA
authors.lastname: del Aguila
authors.forename: Mariola
authors.initials: M
authors.lastname: Tortosa
authors.forename: Alma
authors.initials: A
authors.lastname: Viso
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D006900:Hydroxylation; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D011714:Pyrans; D013454:Sulfoxides; C534161:deoxymalayamicin A; C121741:dysiherbaine; D014498:Uracil; D000409:Alanine